(E)-3-hydroxy-2',4'-dimethoxychalcone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-hydroxy-2',4'-dimethoxychalcone
• 英文别名: (E)-1-(2,4-dimethoxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: OMDOKFLWACHFOE-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-hydroxy-2',4'-dimethoxychalcone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以21%的产率得到(E)-1-(2,4-dihydroxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

  摘要：

  Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as aglucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards aglucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good a-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 mu M concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line). (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.007
• 作为产物：
  描述：

  间羟基苯甲醛 、 2,4-二甲氧基苯乙酮 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以40%的产率得到(E)-3-hydroxy-2',4'-dimethoxychalcone
  参考文献：
  名称：

  Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

  摘要：

  Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as aglucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards aglucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good a-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 mu M concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line). (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.007

文献信息

• Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates
  作者：Chao-Yun Cai、Li Rao、Yong Rao、Jin-Xuan Guo、Zhi-Zun Xiao、Jing-Yu Cao、Zhi-Shu Huang、Bo Wang

  DOI：10.1016/j.ejmech.2017.02.007

  日期：2017.4

  Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as aglucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards aglucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good a-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 mu M concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line). (C) 2017 Elsevier Masson SAS. All rights reserved.